YOU SAID:

The question asker is questioning that question that he is questioning.

INTO JAPANESE

質問者は、彼が質問している質問を質問しています。

BACK INTO ENGLISH

The questioner is asking the question he is asking.

INTO JAPANESE

質問者は、彼が尋ねている質問をしている。

BACK INTO ENGLISH

The interrogator is asking the question he is asking.

INTO JAPANESE

尋問者は、彼が求めている質問をしています。

BACK INTO ENGLISH

The interrogator is asking the question he is asking.